User profile for user: Kikrokos
Kikrokos Author
User level: Level 1
10 points

Attachments cannot be sent with Mail Drop

I cannot send emails with larger attachments anymore.


It used to work out fine, until I updated to macOS 10.15.6 a few days ago. Whenever I try to send an email with pictures of up to 50 MB, I get a notification that attachments can't be sent by Mail Drop, and that I should try later. If I try to send anyway, I get another notification that the message cannot be stored in the 'Outbound' mailbox. The message contains one or more attachments that are supposedly too large to store there.


What's going on? I can send emails with >50 MB attachments from my iPhone, albeit with some caveats. Sending similar emails from the iCloud website works as well, but it takes long to upload the file(s).


Again, until a few days ago, I was fine. I could send emails with >50 MB emails attachments from my iCloud account or other. Now from none. I do have the 'Send large attachments with Mail Drop' checked.

iMac 21.5″, macOS 10.15

Posted on Jul 31, 2020 8:15 AM

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22 replies
User profile for user: jeremy_v
jeremy_v
User level: Community Specialist

Aug 3, 2020 11:24 AM in response to Kikrokos

Kikrokos,


Thanks so much for giving us those additional details.


Since the issue only happens on your Mac, and it does occur when trying to send multiple files to various contacts, we'd like to see if the issue may be related to a user account on your Mac.


This page explains how to test an issue in another user account:


How to test an issue in another user account on your Mac


If the issue doesn't occur when logged into another user account on your Mac, please go through the steps under the "If the issue doesn't happen in the other account" portion of the above link.


Take care!

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User profile for user: i_rina
i_rina
User level: Community Specialist

Aug 3, 2020 9:12 AM in response to Kikrokos

Hi Kikrokos,


We understand that you're experiencing some issues when you try to send emails with attachments over 50 MB, and we'd like to help get to the bottom of what's going on.


Does this happen when sending attachments to all contacts, or just specific ones? We ask because if it only happens when trying to send attachments in emails to certain contacts,  it's possible that the recipient’s email app may have a smaller message size limit that is preventing the attachment from being delivered.


Mail Drop allows you to send attachments up to 5 GB in size. However, there are some situations when attachments may not be sent. Please check out the following link for more information on Mail Drop limits:


Mail Drop limits


For this specific situation, please be sure to review the "Attachments might not be sent using Mail Drop if they exceed these limits" part of the above article, and see if any of those reasons seem to apply.


Thanks!

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User profile for user: i_rina
i_rina
User level: Community Specialist

Aug 3, 2020 12:00 PM in response to Kikrokos

Kikrokos,


We want to make sure you have the information you need, and we'd like to clarify.


While we're unable unable to say what may have caused the change at this point, testing the issue in another user account will allow us to determine if this behavior is related to files or settings in your user account, so that will be very helpful in planning our next steps.


Once you've created a new user account and logged in, you'll need to add your iCloud account to the Mail app, so the issue can be tested in that user account.


Here are those steps for your convenience:


Add an email account to Mail on your Mac


Thank you!

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User profile for user: tygb
tygb
User level: Level 9
65,010 points

Aug 9, 2020 8:19 AM in response to Kikrokos

As per this article https://support.apple.com/en-in/guide/icloud/mm93a9b98683/1.0/icloud/1.0

If you set up iCloud Mail, you can share photos and videos as attachments from your iCloud email.

Note: If the attachments are larger than 20 MB, they are replaced with an iCloud Link.

  1. In Photos on iCloud.com, select the photos or videos you want to share. You can also double-click a single photo or video.
  2. Click the Share button , then choose Email.

share photos using iCloud link .

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User profile for user: tygb
tygb
User level: Level 9
65,010 points

Aug 5, 2020 7:06 AM in response to Kikrokos

As in discussions you wrote - When I look into my 'Sent' folder on my Mac, I can see the previously sent emails to my friend with the comprised versions of the pictures I attached. It says, for example: "Download pictures in full resolution available until August 22nd 2020".


Is your iCloud photo library set up and optimise feature turned as on https://support.apple.com/en-in/HT204264

If you turn on Optimize Storage, iCloud Photos automatically manages the size of your library on your device. Your original photos and videos are stored in iCloud and space-saving versions are kept on your device. Your library is optimized only when you need space, starting with the photos and videos you access least. You can download the original photos and videos over Wi-Fi or cellular when you need them. You can use Optimize Storage on your iPhone, iPad, iPod touch, and Mac.

If you turn on Download Originals, iCloud Photos keeps your original, full-resolution photos and videos in iCloud and on your device.


The settings can be turned as on in cloud.com https://support.apple.com/en-in/guide/icloud/mmb5dbaf376f/1.0/icloud/1.0 or from Mac photos preferences https://support.apple.com/en-in/guide/photos/pht5156cc968/4.0/mac/10.14


Then follow the article https://support.apple.com/en-in/guide/mail/mlhlp1050/mac to attach photos in mail composing window ( see the section Include photos and other files in emails ) .


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User profile for user: JeffGS
JeffGS
User level: Level 1
4 points

Sep 8, 2020 2:09 AM in response to Kikrokos

I too have the same problem that began about 2-3 weeks ago. Both my 5K iMac and MacBook Air run Catalina 10.15.6, Mail Version 13.4 (3608.120.23.2.1) and display the same error below, from all my email accounts and using different user accounts on these Macs. Additionally my iMac main user account Home folder is relocated on another larger data volume (so this made no difference). I also tried unchecking Mail in System_Peferences->Apple_ID->iCloud_Drive then re-enabling it, but no go. Everything else on both Macs are working great - just Mail Drop died without providing any info that we can help to resolve ourselves: Besides not able to send via Mail Drop, while the mail is deciding that it can't be sent, I've seen the Mail Activity monitor claim it's sending 5-7 emails with 5GB to send when the original email included one 50KB attachment, though I retried it 3-4 times. My iCloud is working well except a week ago when there were Worldwide reports of outages. This Mail Drop issue doesn't seem hardware related. I wished there was a fallback if Mail Drop broke and we could simply grab a URL link for a file in our iCloud to drop in our Mail like some other virtual drives, importantly the link is agnostic to any user with/without an iCloud account or a specific email address ? What else can we do to survive large email attachments until Mail Drop is resolved please ?

Thanks, Jeff

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User profile for user: Kikrokos
Kikrokos Author
User level: Level 1
10 points

Aug 3, 2020 11:36 AM in response to jeremy_v

Hello,


Thanks for your response, but I do have some questions. If it's related to my user account (there's no other account on my Mac), why does the issue only occur now? And as I mentioned, although sending multiple files via iCloud website and Mail on my iPhone does work, it takes a lot of time to send the email. Longer than it used to.


Beside, how can I create a different account and still send emails with the Mail app via my iCloud email address? Thanks.

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User profile for user: Kikrokos
Kikrokos Author
User level: Level 1
10 points

Aug 5, 2020 12:40 PM in response to tygb

Hi again,


Thank you both for replying. I will set up the Guest account and iCloud account in the Mail app as soon as I get back home.


I do like to make a comment on sending emails with >50 MB attachments from my iPhone between my own email addresses. I noticed it will be sent from the Mail app on my iPhone, but it takes some time. When I receive the email in the same Mail app (on my iPhone or my Mac), the attached pictures are suddenly comprised to <10 MB. I'd like to remind you that I did opt for 'Original size' upon sending.


Regarding the iCloud photo library set up: it's not set to 'optimized only'. Moreover, this is not applicable here, because the pictures I attach in my email do not originate from my iCloud photo library. But thanks anyway!

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User profile for user: Kikrokos
Kikrokos Author
User level: Level 1
10 points

Aug 7, 2020 1:22 AM in response to tygb

Guest account or admin account: neither of them work. I don't use VPN services, anti virus or anything you mention.


Again, I need to repeat this because I don't feel like you're taking this into account: everything worked fine until a week ago. Moreover: other files I can attach and send perfectly fine with the Mail app. It's just image files (photos/pictures) from any source that doesn't work all of a sudden.


It all happened since I updated to version 10.15.6. That's the only connection I can think of.

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User profile for user: Kikrokos
Kikrokos Author
User level: Level 1
10 points

Aug 7, 2020 1:43 AM in response to tygb

This is impossible. I choose my iMac, then I pick Mail from the options. But whether I opt for chat or call: I have to 'ask for an exception', since my Mac is already 10 months old. And if I do that, I get a menu I have to pick from, but none of the situations applies to me. So there's no way to get in touch with Apple Support. This makes me sad.

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User profile for user: Kikrokos
Kikrokos Author
User level: Level 1
10 points

Aug 16, 2020 9:07 AM in response to tygb

When I log on to icloud.com. create a new email and attach pictures from Photos, iCloud immediately creates a link of these pictures >20 MB. This email will be send seamlessly. But how can I get this working again in the Mail app? Attaching >20 MB of photos from the Photos app to an email in the Mail app doesn't work, let alone pictures/photos from other sources.


For those of you just joining, here's what's going on.


Until a few weeks ago, I could send 50 MB of photos from any source as attachment to an email via the Mail app on my Mac, easily. To any recipient and with no issues at all.


Now, I cannot do this anymore. Whether I use photos from iCloud/Photos app or from my Mac or right from the internet: it doesn't work with photo attachments >20 MB. I get a an error notification that says the attachments cannot be send with Mail Drop. If I subsequently try to save the email to the outgoing email folder, it says it cannot store it there either.


Whatever I choose, Mail still tries to send the email with the >20 MB of photos, as visible from the status bar in the left hand corner of the Mail app. But it never completes this task.


It's not an issue on the side of the recipient, because I tried several. 'Sending large attachments with Mail Drop' is selected in Mail preferences. And most of all: it worked seamlessly in the past. Only difference is MacOS update 10.15.6. After that, the issue started.


Furthermore, I can still send other large attachments via the Mail app just fine, like mp3 files or pdf docs.


Someone who can help me out here?

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Attachments cannot be sent with Mail Drop

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